Thioxothienopyrimidinones, alkylthio-and arylalkylthiothienopyrimidinones, thienopyrimidinones, thienopyrimidines a thienopyrimidinedione and a thienotriazolopyrimidinone were prepared from 2-amino-3-carboethoxy-4,5-disubstituted thiophenes and 2-amino-3-cyano-4,5-disubstituted thiophenes via reactions with different reagents.
The conditions of the reaction of malononitrile dimer with enaminones and arylidenemalononitrile could be adapted to yield either pyridines or benzene derivatives. A new synthesis of pyrido[1,2-a]pyrimidines from the reaction of malononitrile dimer 1 and 2-phenyl-3-piperidin-1-yl-acrylonitrile (11) is described. Compound 1 condensed with DMFDMA to yield an enaminonitrile that reacted with hydrazine hydrate to yield N',4,6-triamino-2H-pyrazolo[3,4-b]pyridine-5-carboxamidine (17).
Treatment of anthranilic acid 1 or 3-amino 2-naphthoic acid 5 with butyl isocyanate in THF led to the formation of the ureido derivatives 3 and 7 respectively, which were cyclized to the corresponding diones 4 and 8 by refluxing in DMF, while the treatment of 1 or 5 with butyl isocyanate in DMF afforded the same diones 4 and 8 respectively. Treatment of 2,4-Bis (trimethylsilyloxy) quinazoline 9 with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)quinazoline-2,4(1H-3H)-dione 11. Debenzolation led to the free nucleoside 12. Structural proofs of the prepared compounds are based on spectroscopic methods.
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